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US4960874A - Isothiazolylazo dyes having aminophenyl and aminonaphthyl components - Google Patents

Isothiazolylazo dyes having aminophenyl and aminonaphthyl components Download PDF

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US4960874A
US4960874A US07/214,502 US21450288A US4960874A US 4960874 A US4960874 A US 4960874A US 21450288 A US21450288 A US 21450288A US 4960874 A US4960874 A US 4960874A
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substituted
alkyl
formula
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Udo Bergmann
Johannes D. Dix
Guenter Hansen
Ernst Schefczik
Guenther Seybold
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
    • C09B29/0847—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 substituted by halogen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
    • C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
    • C09B29/0081—Isothiazoles or condensed isothiazoles
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0805—Amino benzenes free of acid groups
    • C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
    • C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
    • C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
    • C09B29/0813—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0805—Amino benzenes free of acid groups
    • C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
    • C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
    • C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
    • C09B29/083—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino having -N< (in a ring)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/095—Amino naphthalenes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S534/00—Organic compounds -- part of the class 532-570 series
    • Y10S534/02—Azo compounds containing chains of eight or more carbon atoms not provided for elsewhere in this class

Definitions

  • the present invention relates to compounds of the general formula I ##STR3## where R is alkyl or unsubstituted or substituted aryl and K is a radical of the formula ##STR4##
  • B is C 1 -C 4 -alkyl or substituted amino
  • R 1 is hydrogen, methyl, methoxy or ethoxy
  • R 2 and R 3 independently of one another are each unsubstituted or substituted alkyl
  • R 3 may furthermore be hydrogen
  • R 4 is a radical of the formula --A--OCO--Y--R
  • Z is hydrogen or methyl
  • X is hydrogen, methyl, methoxy, chlorine or acylamino
  • A is C 2 - or C 3 -alkylene and Y is --O-- or --NH---.
  • Alkyl R is preferably of 1 to 8 carbon atoms, specific examples being methyl, ethyl, n-propyl, i-propyl, butyl, hexyl and 2-ethylhexyl.
  • Unsubstituted or substituted aryl radicals R are, for example, ##STR5##
  • Substituted amino radicals B are, for example, N(CH 3 ) 2 , N(C 2 H 5 ) 2 , ##STR6##
  • R 2 and R 3 are, for example, alkyl which is of 1 to 4 carbon atoms and can be substituted by chlorine, bromine, cyano, hydroxyl, C 1 -C 4 -alkyoxy, benzyloxy, phenoxy, phenyl, C 1 -C 4 -alkylcarbonyloxy which may be unsubstituted or further substituted by C 1 -C 4 -alkoxy, phenoxy or phenyl, phenylcarbonyloxy which is unsubstituted or substituted by Cl, Br, OCH 3 , OC 2 H 5 , CH 3 or C 2 H 5 , oxycarbonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyloxy, carbamyl, phenalkyloxycarbonyloxy, phenoxyalkyloxycarbonyloxy, C 1 -C 4 -alkoxyal
  • R 4 is ##STR8##
  • R 2 and R 4 together can form a saturated heterocyclic ring, e.g. a piperidine or morpholine ring.
  • acylamino radicals X are NH--CHO, NHCOCH 3 , NHCOC 2 H 5 , NH--CO-aryl, NHCOCH 2 -aryl, ##STR9## and CO--CH 2 --O--CH 3 .
  • the compounds of the formula I can be prepared by reacting a diazonium compound of an amine of the formula ##STR10## with a coupling component of the formula
  • the compounds of the formula I are useful for dyeing cellulose esters and in particular synthetic polyesters; the dyeings obtained are from yellow to blue, and as a rule very fast. It may be advantageous to use a mixture of compounds of the formula I for this purpose.
  • K 1 is a radical of the formula ##STR12##
  • B 1 is C 1 -C 4 -alkyl, and R, R 1 , R 2 , R 3 , R 4 and X have the above meanings.
  • R 1 is preferably H, CH 3 or OCH 3
  • R 2 is preferably CH 3 , C 2 H 5 , C 3 H 7 , C 4 H 9 , C 2 H 4 CN, C 2 H 4 OH, CH 2 --CHOHCH 3 , ##STR13##
  • the diazonium salt solution thus obtained was allowed to run slowly into a mixture of 11.2 parts of N-ethyl-N-methoxycarbonyloxyethylaniline, 20 parts by volume of 32 percent strength hydrochloric acid, 250 parts of water, 250 parts of ice and one part of amidosulfonic acid. After coupling was complete, the product was filtered off under suction, washed neutral and dried under reduced pressure at 50° C. to give 16.5 parts of the dye of the formula ##STR14## This dye dyes polyester fibers in fast, clear bluish red hues.
  • a diazo solution prepared as described in Example 1 from 7 parts of 5-amino-4-cyano-3-methylisothiazole was added to a mixture of 16 parts of N-ethyl-N, ⁇ -phenylethoxycarbonyloxyethylaniline, 30 parts by volume of 32% strength hydrochloric acid, 250 parts of water and 250 parts of ice. After coupling was complete, the product was filtered off under suction, washed neutral, and dried under reduced pressure at 50° C. to give 18.8 parts of the dye of the formula ##STR15## This dye dyes polyesters in bluish red hues.
  • the diazo solution thus obtained was added dropwise to a mixture of 15.7 parts of 4-chloro-3-methoxyethoxycarbonylethylaminoacetanilide, 30 parts by volume of 32% strength hydrochloric acid, 250 parts of ice, 250 parts of water and one part of amidosulfonic acid. After coupling was complete, the product was filtered off under suction, washed neutral and dried under reduced pressure at 50° C. to give 21.9 parts of the dye of the formula ##STR18## This dye dyes polyesters in fast bluish red hues.
  • a diazonium salt solution prepared as described in Example 5 from 10.1 parts of 5-amino-4-cyano-3-phenylisothiazole was added dropwise to a mixture of 16.8 parts of N-cyanoethyl-N-ethoxyethoxycarbonyloxyethylaniline, 20 parts by volume of 32% strength hydrochloric acid, 250 parts of water, 250 parts of ice and one part of amidosulfonic acid. After coupling was complete, the product was filtered off under suction, washed neutral, and dried under reduced pressure at 50° C. to give 21.3 parts of the dye of the formula ##STR19## This dye dyes polyesters in fast red hues.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

Compounds of the general formula I ##STR1## where R is alkyl or unsubstituted or substituted aryl and K is a radical of the formula ##STR2## B is C1 -C4 -alkyl or substituted amino, R1 is hydrogen, methyl, methoxy or ethoxy, R2 and R3 independently of one another are each unsubstituted or substituted alkyl, R3 may furthermore be hydrogen, R4 is a radical of the formula --A--OCO--Y--R, Z is hydrogen or methyl, X is hydrogen, methyl, methoxy, chlorine or acylamino, A is C2 - or C3 -alkylene and Y is --O-- or --NH--, are very useful for dyeing cellulose esters and synthetic polyesters.

Description

This is a continuation, of application Ser. No. 06/460,793, filed Jan. 25, 1983, now U.S. Pat. No. 4,764,600.
The present invention relates to compounds of the general formula I ##STR3## where R is alkyl or unsubstituted or substituted aryl and K is a radical of the formula ##STR4## B is C1 -C4 -alkyl or substituted amino, R1 is hydrogen, methyl, methoxy or ethoxy, R2 and R3 independently of one another are each unsubstituted or substituted alkyl, R3 may furthermore be hydrogen, R4 is a radical of the formula --A--OCO--Y--R, Z is hydrogen or methyl, X is hydrogen, methyl, methoxy, chlorine or acylamino, A is C2 - or C3 -alkylene and Y is --O-- or --NH--.
Alkyl R is preferably of 1 to 8 carbon atoms, specific examples being methyl, ethyl, n-propyl, i-propyl, butyl, hexyl and 2-ethylhexyl.
Unsubstituted or substituted aryl radicals R are, for example, ##STR5## Substituted amino radicals B are, for example, N(CH3)2, N(C2 H5)2, ##STR6##
Unsubstituted or substituted alkyl radicals R2 and R3 are, for example, alkyl which is of 1 to 4 carbon atoms and can be substituted by chlorine, bromine, cyano, hydroxyl, C1 -C4 -alkyoxy, benzyloxy, phenoxy, phenyl, C1 -C4 -alkylcarbonyloxy which may be unsubstituted or further substituted by C1 -C4 -alkoxy, phenoxy or phenyl, phenylcarbonyloxy which is unsubstituted or substituted by Cl, Br, OCH3, OC2 H5, CH3 or C2 H5, oxycarbonyl, C1 -C4 -alkoxycarbonyl, C1 -C4 -alkoxycarbonyloxy, carbamyl, phenalkyloxycarbonyloxy, phenoxyalkyloxycarbonyloxy, C1 -C4 -alkoxyalkoxycarbonyloxy, phenylaminocarbonyloxy which is unsubstituted or substituted by Cl, methoxy or methyl, C1 -C4 -alkoxyalkoxycarbonyl, phenylalkyloxycarbonyl or C1 -C4 -alkylaminocarbonyloxy which is unsubstituted or substituted by C1 -C4 -alkyl, C1 -C4 -alkoxy, chlorine or bromine.
Specific examples of such radicals are: ##STR7##
Specific examples of R4 are ##STR8##
R2 and R4 together can form a saturated heterocyclic ring, e.g. a piperidine or morpholine ring.
Examples of acylamino radicals X are NH--CHO, NHCOCH3, NHCOC2 H5, NH--CO-aryl, NHCOCH2 -aryl, ##STR9## and CO--CH2 --O--CH3.
The compounds of the formula I can be prepared by reacting a diazonium compound of an amine of the formula ##STR10## with a coupling component of the formula
H-K
In the Examples which follow, and illustrate the invention, parts and percentages are by weight, unless stated otherwise.
The compounds of the formula I are useful for dyeing cellulose esters and in particular synthetic polyesters; the dyeings obtained are from yellow to blue, and as a rule very fast. It may be advantageous to use a mixture of compounds of the formula I for this purpose.
Of particular industrial importance are compounds of the formula I a ##STR11## where K1 is a radical of the formula ##STR12## B1 is C1 -C4 -alkyl, and R, R1, R2, R3, R4 and X have the above meanings.
R1 is preferably H, CH3 or OCH3, and R2 is preferably CH3, C2 H5, C3 H7, C4 H9, C2 H4 CN, C2 H4 OH, CH2 --CHOHCH3, ##STR13##
EXAMPLE 1
7 parts of 5-amino-4-cyano-3-methylisothiazole were dissolved in 75 parts by volume of a mixture of 17 parts of glacial acetic acid and 3 parts of propionic acid, 20 parts of 85% strength sulfuric acid were added, 16 parts of nitrosylsulfuric acid (11.5% of N2 O3) were allowed to run in slowly into the stirred mixture at 0°-5° C., and stirring was continued at this temperature for 4 hours. The diazonium salt solution thus obtained was allowed to run slowly into a mixture of 11.2 parts of N-ethyl-N-methoxycarbonyloxyethylaniline, 20 parts by volume of 32 percent strength hydrochloric acid, 250 parts of water, 250 parts of ice and one part of amidosulfonic acid. After coupling was complete, the product was filtered off under suction, washed neutral and dried under reduced pressure at 50° C. to give 16.5 parts of the dye of the formula ##STR14## This dye dyes polyester fibers in fast, clear bluish red hues.
EXAMPLE 2
A diazo solution prepared as described in Example 1 from 7 parts of 5-amino-4-cyano-3-methylisothiazole was added to a mixture of 16 parts of N-ethyl-N,β-phenylethoxycarbonyloxyethylaniline, 30 parts by volume of 32% strength hydrochloric acid, 250 parts of water and 250 parts of ice. After coupling was complete, the product was filtered off under suction, washed neutral, and dried under reduced pressure at 50° C. to give 18.8 parts of the dye of the formula ##STR15## This dye dyes polyesters in bluish red hues.
EXAMPLE 3
11.1 parts of N-ethyl-N-propylaminocarbonyloxyethylaniline in 10 parts by volume of dimethylformamide and 20 parts by volume of 32% strength hydrochloric acid were added to a mixture of 250 parts of water, 250 parts of ice and one part of amidosulfonic acid. A diazonium salt solution prepared as described in Example 1 was allowed to run slowly into the above mixture. After coupling was complete, the product was filtered off under suction, washed neutral and dried under reduced pressure at 20° C. to give 17.2 parts of the dye of the formula ##STR16## This dye dyes polyesters in clear bluish red hues.
EXAMPLE 4
14.2 parts of N-ethyl-N-phenylaminocarbonyloxyethylaniline in 8 parts by volume of dimethylformamide and 30 parts by volume of hydrochloric acid were coupled, by a procedure similar to that described in Example 3, with the diazonium salt obtained from 7 parts of 5-amino-4-cyano-3-methylisothiazole. After the product had been dried, 20.3 parts of the dye of the formula ##STR17## were obtained. This dye dyes polyester fibers in bluish red hues.
EXAMPLE 5
16 parts of nitrosylsulfuric acid (11.5% of N2 O3) were added slowly to 10.1 parts of 5-amino-4-cyano-3-phenylisothiazole in a mixture of 75 parts by volume of glacial acetic acid/propionic acid (17:3 v/v) and 20 parts by volume of 85% strength sulfuric acid at 0°-5° C., while stirring, and stirring was continued for 4 hours at this temperature. The diazo solution thus obtained was added dropwise to a mixture of 15.7 parts of 4-chloro-3-methoxyethoxycarbonylethylaminoacetanilide, 30 parts by volume of 32% strength hydrochloric acid, 250 parts of ice, 250 parts of water and one part of amidosulfonic acid. After coupling was complete, the product was filtered off under suction, washed neutral and dried under reduced pressure at 50° C. to give 21.9 parts of the dye of the formula ##STR18## This dye dyes polyesters in fast bluish red hues.
EXAMPLE 6
A diazonium salt solution prepared as described in Example 5 from 10.1 parts of 5-amino-4-cyano-3-phenylisothiazole was added dropwise to a mixture of 16.8 parts of N-cyanoethyl-N-ethoxyethoxycarbonyloxyethylaniline, 20 parts by volume of 32% strength hydrochloric acid, 250 parts of water, 250 parts of ice and one part of amidosulfonic acid. After coupling was complete, the product was filtered off under suction, washed neutral, and dried under reduced pressure at 50° C. to give 21.3 parts of the dye of the formula ##STR19## This dye dyes polyesters in fast red hues.
The compounds below were prepared by similar procedures.
__________________________________________________________________________
Example                                                                   
     R         K                      Hue on polyesters                   
__________________________________________________________________________
 7   CH.sub.3                                                             
                ##STR20##             bluish red                          
 8   "                                                                    
                ##STR21##             "                                   
 9   "                                                                    
                ##STR22##             "                                   
10   "                                                                    
                ##STR23##             "                                   
11   "                                                                    
                ##STR24##             "                                   
12   "                                                                    
                ##STR25##             "                                   
13   "                                                                    
                ##STR26##             "                                   
14   "                                                                    
                ##STR27##             "                                   
15   "                                                                    
                ##STR28##             violet                              
16   CH.sub.3                                                             
                ##STR29##             red                                 
17   "                                                                    
                ##STR30##             "                                   
18   "                                                                    
                ##STR31##             bluish red                          
19   "                                                                    
                ##STR32##             yellowish red                       
20   "                                                                    
                ##STR33##             "                                   
21   "                                                                    
                ##STR34##             "                                   
22                                                                        
      ##STR35##                                                           
                ##STR36##             "                                   
23   "                                                                    
                ##STR37##             "                                   
24                                                                        
      ##STR38##                                                           
                ##STR39##             red                                 
25   "                                                                    
                ##STR40##             bluish red                          
26   "                                                                    
                ##STR41##             "                                   
27   "                                                                    
                ##STR42##             "                                   
28   "                                                                    
                ##STR43##             "                                   
29   "                                                                    
                ##STR44##             "                                   
30   "                                                                    
                ##STR45##             bluish red                          
31   "                                                                    
                ##STR46##             "                                   
32                                                                        
      ##STR47##                                                           
                ##STR48##             bluish red                          
33   "                                                                    
                ##STR49##             red                                 
34   "                                                                    
                ##STR50##             bluish red                          
35   "                                                                    
                ##STR51##             "                                   
36   "                                                                    
                ##STR52##             "                                   
37                                                                        
      ##STR53##                                                           
                ##STR54##             yellowish red                       
38   "                                                                    
                ##STR55##             red                                 
39   "                                                                    
                ##STR56##             bluish red                          
40                                                                        
      ##STR57##                                                           
                ##STR58##             bluish red                          
41   "                                                                    
                ##STR59##             red                                 
42   "                                                                    
                ##STR60##             "                                   
43   "                                                                    
                ##STR61##             "                                   
44   "                                                                    
                ##STR62##             yellowish red                       
45   "                                                                    
                ##STR63##             "                                   
46                                                                        
      ##STR64##                                                           
                ##STR65##             red                                 
47   "                                                                    
                ##STR66##             bluish red                          
48                                                                        
      ##STR67##                                                           
                ##STR68##             bluish red                          
49   "                                                                    
                ##STR69##             "                                   
50   "                                                                    
                ##STR70##             red                                 
51   "                                                                    
                ##STR71##             bluish red                          
52   "                                                                    
                ##STR72##             red                                 
53   CH.sub.3                                                             
                ##STR73##             blue                                
54   "                                                                    
                ##STR74##             bluish red                          
55   "                                                                    
                ##STR75##             violet                              
56   CH.sub.3                                                             
                ##STR76##             red                                 
57                                                                        
      ##STR77##                                                           
                ##STR78##             bluish red                          
58   "                                                                    
                ##STR79##             red                                 
59                                                                        
      ##STR80##                                                           
                ##STR81##             violet                              
60   "                                                                    
                ##STR82##             "                                   
61   "                                                                    
                ##STR83##             "                                   
62                                                                        
      ##STR84##                                                           
                ##STR85##             bluish red                          
63   "                                                                    
                ##STR86##             "                                   
64   "                                                                    
                ##STR87##             "                                   
65   "                                                                    
                ##STR88##             violet                              
66   "                                                                    
                ##STR89##             "                                   
67                                                                        
      ##STR90##                                                           
                ##STR91##             violet                              
68   "                                                                    
                ##STR92##             "                                   
69   "                                                                    
                ##STR93##             bluish red                          
70   CH(CH.sub.3).sub.2                                                   
                ##STR94##             red                                 
71   "                                                                    
                ##STR95##             "                                   
72   "                                                                    
                ##STR96##             "                                   
73   CH(CH.sub.3).sub.2                                                   
                ##STR97##             red                                 
74   "                                                                    
                ##STR98##             bluish red                          
75   "                                                                    
                ##STR99##             red                                 
76   "                                                                    
                ##STR100##            red                                 
77   "                                                                    
                ##STR101##            red                                 
78   CH(CH.sub.3).sub.2                                                   
                ##STR102##            bluish red                          
79   "                                                                    
                ##STR103##            "                                   
80   "                                                                    
                ##STR104##            red                                 
81   CH.sub.3                                                             
                ##STR105##            violet                              
82   "                                                                    
                ##STR106##            "                                   
83   CH.sub.3                                                             
                ##STR107##            bluish red                          
84   "                                                                    
                ##STR108##            "                                   
85   "                                                                    
                ##STR109##            "                                   
__________________________________________________________________________

Claims (5)

We claim:
1. An isothiazolylazo dye of the formula: ##STR110## wherein R is alkyl or unsubstituted aryl radical or a substituted aryl radical of the formula: ##STR111## and K is a radical of the formula: ##STR112## wherein B is C1 -C4 alkyl or a substituted amino radical selected from the group consisting of: ##STR113## where R1 is hydrogen, methyl, methoxy or ethoxy, R2 and R3 independently of one another are each unsubstituted C1 -C4 alkyl or substituted alkyl groups selected from the group consisting of C1 -C4 alkyls which are substituted by chlorine, bromine, cyano, hydroxyl, C1 -C4 alkoxy, benzyloxy, phenoxy, phenyl, C1 -C4 -alkylcarbonyloxy which is unsubstituted or further substituted by C1 -C4 alkoxy, phenoxy or phenyl, or phenylcarbonyloxy which is unsubstituted or substituted by chlorine, bromine, methoxy, ethoxy, methyl or ethyl, oxycarbonyl, C1 -C4 alkoxycarbonyl, C1 -C4 alkoxycarbonyloxy, carbamyl, phenylalkoxycarbonyloxy, phenoxyalkyloxycarbonyloxy, C1 -C4 alkoxyalkoxycarbonyloxy, phenylaminocarbonyloxy which is unsubstituted or substituted by chlorine, methoxy or methyl, C1 -C4 alkoxyalkoxycarbonyl, phenylalkyloxycarbonyl or C1 -C4 alkylaminocarbonyloxy which is unsubstituted or substituted by C1 -C4 alkyl, C1 -C4 alkoxy, chlorine or bromine; or R3 is hydrogen, R4 is a radical of the formula --A--OCO--Y-- R, Z is hydrogen or methyl, X is hydrogen, methyl or methoxy or an acylamino radical selected from the group consisting of:
--NHCHO, --NHCOCH3, --NHCOC2 H5, --NHCO-aryl,
--NHCOCH2 -aryl or ##STR114## or --COCH2 --O--CH3, A is C2 - or C3 -alkylene and Y is --O-- or --NH--.
2. The dye as claimed in claim 1, of the formula ##STR115## where K1 is a radical of the formula ##STR116## where B1 is C1 -C4 alkyl and R, R1, R2, R3, R4 and X have the above meanings.
3. The dye as claimed in claim 1, wherein R is methyl, ethyl, i-propyl, n-propyl, butyl, hexyl or 2-ethylhexyl or is phenyl which is unsubstituted or substituted by methyl, methoxy, ethoxy or chlorine.
4. The dye as claimed in claim 1, wherein R2 is a straight-chain or branched C1 -C4 alkyl and R3 is hydrogen or a straight-chain or branched C1 -C4 alkyl, or is a C1 -C4 which is substituted by hydroxyl, C1 -C4 alkanoyloxy, C1 -C4 alkoxycarbonyl, C1 -C4 alkoxycarbonyloxy, C1 -C4 alkylaminocarbonyloxy, phenylaminocarbonyloxy, chlorophenylaminocarbonyloxy, cyano or phenyl.
5. The dye as claimed in claim 2, wherein R1 is H, CH3 or OCH3 ; and R2 is CH3, C2 H5, C3 H7, C4 H9, C2 H4, CN, C2 H4 OH, CH2 CHOHCH3, CH2 CHOHC2 H5, C3 H6 OCH3, ##STR117##
US07/214,502 1982-02-16 1988-07-01 Isothiazolylazo dyes having aminophenyl and aminonaphthyl components Expired - Lifetime US4960874A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6187084B1 (en) * 1998-03-31 2001-02-13 Zeneca Ltd. Ink compositions
US6197223B1 (en) 1996-11-27 2001-03-06 Eastman Chemical Company Method for preparing light-absorbing polymeric compositions
US20080119644A1 (en) * 2003-04-24 2008-05-22 Xerox Corporation Colorant compositions

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3205435A1 (en) * 1982-02-16 1983-08-25 Basf Ag, 6700 Ludwigshafen ISOTHIAZOLAZO DYES
DE3400364A1 (en) * 1984-01-07 1985-07-18 Basf Ag, 6700 Ludwigshafen ISOTHIAZOLAZO DYES
DE3409243A1 (en) * 1984-03-14 1985-09-19 Basf Ag, 6700 Ludwigshafen ISOTHIAZOLAZO DYES
DE3427201A1 (en) * 1984-07-24 1986-01-30 Basf Ag, 6700 Ludwigshafen HETEROCYCLIC AZO DYES
DE3810643A1 (en) * 1988-03-29 1989-10-12 Basf Ag ISOTHIAZOLAZO DYES
US5144015A (en) * 1990-12-21 1992-09-01 Eastman Kodak Company Synthesis of pyrazole dyes

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2771466A (en) * 1953-02-13 1956-11-20 Eastman Kodak Co 5-nitrothiazoleazo-n, n-disubstituted m-alkacylaminoaniline compounds
GB1379233A (en) * 1971-03-01 1975-01-02 Ici Ltd Disperse monoazo dyestuffs
US3997520A (en) * 1973-07-17 1976-12-14 Sandoz Ltd. 5-Nitrothiazolyl-2-azophenyl disperse dyes
GB2041391A (en) * 1979-01-30 1980-09-10 Sandoz Ltd Improvements in or relating to monoazo dyes
US4225490A (en) * 1971-06-17 1980-09-30 Sandoz Ltd. Heterocyclyl-azo-phenyl dyes having a cationic group linked through a branched alkylene chain to the nitrogen atom of the coupling component radical
US4324899A (en) * 1979-07-05 1982-04-13 Eastman Kodak Company 2-Amino-5-cyanothiazoles and their preparation
US4330467A (en) * 1980-03-03 1982-05-18 Eastman Kodak Company Disubstituted isothiazole azo dyes containing tetrahydroquinoline type couplers
US4354970A (en) * 1980-03-07 1982-10-19 Eastman Kodak Company Indoline coupled isothiazole azo dyes
US4374768A (en) * 1980-06-16 1983-02-22 Eastman Kodak Company Disperse dyes from 5-amino-4-halo-3-methylisothiazoles
US4382801A (en) * 1980-12-24 1983-05-10 Ciba-Geigy Corporation Process for spin dyeing polymers or copolymers of acrylonitrile with quaternized heterocyclic diazo dye and tetrafluoro-borate anion
US4764600A (en) * 1982-02-16 1988-08-16 Basf Aktiengesellschaft Isothiazolylazo dyes having aminophenyl and aminonaphthyl components

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2771466A (en) * 1953-02-13 1956-11-20 Eastman Kodak Co 5-nitrothiazoleazo-n, n-disubstituted m-alkacylaminoaniline compounds
GB1379233A (en) * 1971-03-01 1975-01-02 Ici Ltd Disperse monoazo dyestuffs
US4225490A (en) * 1971-06-17 1980-09-30 Sandoz Ltd. Heterocyclyl-azo-phenyl dyes having a cationic group linked through a branched alkylene chain to the nitrogen atom of the coupling component radical
US3997520A (en) * 1973-07-17 1976-12-14 Sandoz Ltd. 5-Nitrothiazolyl-2-azophenyl disperse dyes
GB2041391A (en) * 1979-01-30 1980-09-10 Sandoz Ltd Improvements in or relating to monoazo dyes
US4324899A (en) * 1979-07-05 1982-04-13 Eastman Kodak Company 2-Amino-5-cyanothiazoles and their preparation
US4330467A (en) * 1980-03-03 1982-05-18 Eastman Kodak Company Disubstituted isothiazole azo dyes containing tetrahydroquinoline type couplers
US4354970A (en) * 1980-03-07 1982-10-19 Eastman Kodak Company Indoline coupled isothiazole azo dyes
US4374768A (en) * 1980-06-16 1983-02-22 Eastman Kodak Company Disperse dyes from 5-amino-4-halo-3-methylisothiazoles
US4382801A (en) * 1980-12-24 1983-05-10 Ciba-Geigy Corporation Process for spin dyeing polymers or copolymers of acrylonitrile with quaternized heterocyclic diazo dye and tetrafluoro-borate anion
US4764600A (en) * 1982-02-16 1988-08-16 Basf Aktiengesellschaft Isothiazolylazo dyes having aminophenyl and aminonaphthyl components

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6197223B1 (en) 1996-11-27 2001-03-06 Eastman Chemical Company Method for preparing light-absorbing polymeric compositions
US6776930B2 (en) 1996-11-27 2004-08-17 Eastman Kodak Company Method for preparing light-absorbing polymeric compositions
US20040195552A1 (en) * 1996-11-27 2004-10-07 Weaver Max Allen Method for preparing light-absorbing polymeric compositions
US6187084B1 (en) * 1998-03-31 2001-02-13 Zeneca Ltd. Ink compositions
US20080119644A1 (en) * 2003-04-24 2008-05-22 Xerox Corporation Colorant compositions

Also Published As

Publication number Publication date
JPS58171448A (en) 1983-10-08
EP0087616B1 (en) 1986-02-05
JPH049191B2 (en) 1992-02-19
DE3205435A1 (en) 1983-08-25
EP0087616A1 (en) 1983-09-07
US4764600A (en) 1988-08-16
DE3362043D1 (en) 1986-03-20

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